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Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!
- Punta Gorda, FL
- Crooner
- Travels nationwide
- Contact for rates
Overview
Hi, Troy Chiappone here, if you are planning a once-in-a-lifetime event for your special someone such as: a marriage proposal, wedding first dance, cocktail hour, birthday party, anniversary, or bachelorette party, then make it a fantastic memory full of smiles and fun with my singing telegram, or my 1 - 3 hour performances. I'm not afraid to walk right up to my guest and serenade them personally (I also offer my singing at funerals as a memorial to honor loved ones)
I always arrive at your event on time, I bring excellent sounding music equipment & wireless microphone, I dress sharp in a 007-style tuxedo or otherwise, and I perform some of the best songs of all-time by legendary artists.
28 Reviews
Love the song selections!!! Fun performance and enjoyable selections!!
Crooner, Italian Entertainment
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thank you so much Susan! I had a fantastic time and enjoyed the people there.
Troy came to celebrate my grandmothers 92nd birthday. It was amazing! Just the best birthday gift ever. He sang some Nat King Cole and Frank Sinatra among others. My grandparents smiled and sang along and danced, just like the good ole days. Troy was great to work with, very accommodating and flexible. We had to change the date very last minute, not a problem. He suggested zooming with out of town family so they could all be apart of it. I cannot recommend Troy enough. You will not be disappointed. Do your loved one and self a favor, book Troy!!
Singing Telegram
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
I really had a fantastic time too! It's such a blessing to be able to make people happy such as yourselves and your grandparents! Thank you for choosing me :)
Troy has a pure and positive energy, and an INCREDIBLE voice! He is forever an icon in me & my family’s life. We are so grateful for him and his talent!
Frank Sinatra Impersonator, Italian Entertainment
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
You were a blast to dance with and are uber sweet to leave me a review here as well. Thank you so much 💞
My siblings and I hired Troy to suprise our mother as Elvis. He was flexible (we asked him to come to the rec center in her neighborhood and sing during Bunco) on point (he had a fabulous black leather outfit and high quality portable sound system he carried in with professional backing tracks), responsive (we live in MA and mom lives in FL)--Troy and I texted back and forth working out minor details, and his contract was clear and detailed. His voice was terrific and he will likely get some other bookings. My mom wants to know where he is performing next so she can get tickets! Thank you for making my mom (and the Bunco ladies) the talk of the town.
Las Vegas Style Entertainment, Singing Telegram
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thank you so much Amy you are super sweet for doing this and it was a joy to work with you, and a fun performance!
Troy is a great guy and an outstanding entertainer. We booked Troy to help make an 80th birthday memorable. He was great from the get go, extremely patient with us as we tried to organize/schedule the birthday surprise. Easy to communicate and work with in order to make sure the event was a success. The recipient was over the moon with her surprise singing telegram. His performance brought the birthday girl to tears (of happiness) and she’s still raving about it! A total success from planning to execution. Don’t hesitate just book him!
Frank Sinatra Impersonator, Italian Entertainment, Singing Telegram
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thank you so much for the thoughtful and kind words Nancy! It was a beautiful and fun group and you were truly a pleasure to work with!
Troy was amazing from the minute he walked singing through the front door surprising all our guests. It was awesome all the way through… We have to give Troy five stars, first class person, and act! Highly recommend.
Italian Entertainment
Communicated well and provided everything as requested. Would recommend.
Dean Martin Impersonator
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thank you so much Becky! And Happy Valentine's!
Troy was very helpful, and the recipient was happily surprised! Great job!
Crooner
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thank you so much for the five star review Dave! I had a fantastic time and it was such a privilege to get the birthday girl to smile and have some fun before another day of work. Cheers🍹🤗
Troy was phenomenal! He kept the dance floor full all night long. He played all request and the crowd loved him. He’s very professional, personable, charming and handsome, the ladies loved him. We will not hesitate to have him return! Thank you again Troy 😊
Dean Martin Impersonator, Frank Sinatra Impersonator
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thank you so much Sandy! You just made my day and I am glad I helped make NYE lots of fun for you and the rest of the bunch. 🙏🤗🎉
Troy is very personable and entertained for my husbands 70th bday party. Everyone had a ball…ages 2-70.
Dean Martin Impersonator, Frank Sinatra Impersonator, Italian Entertainment, Crooner
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thank you so much Ellie a review like this helps me out immensely! your cheesecake was superb and your family is beautiful! I hope your New Years weekend is a joy.
I just wanted to give a big shout out to Troy. Troy performed at my husbands 60th birthday party which really made the night complete. He sang Frank Sinatra and many other tunes. He arrived early, organized and was very engaging with the party guests. My husband and the party guests really enjoyed him entertaining us. If you looking for someone I would recommend Troy. Thanks again. April
Troy was profesional, punctual, and talented anyone who is looking for perfect singing telegram he is your man. Thank you, Troy for making our 80 year girl feel really special on her birthday.
1930s Era Entertainment, Big Band, Broadway Style Entertainment, Dean Martin Impersonator, Frank Sinatra Impersonator, Italian Entertainment, Jazz Singer, Las Vegas Style Entertainment, Rat Pack Tribute Show, Singing Telegram, Wedding Band, Wedding Singer, Crooner
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thanks a lot for the kind words my man! I enjoyed meeting everyone especially the birthday girl!
Troy did an amazing performance for our event. Our event was for a very small group of people. Troy made it very special for our guest of honor, he touched her heart. I would highly recommend Troy and Gigsalad. Communication was great and punctual. You will be pleased.
We hired Troy Chiappone to sing at my mom’s 80th birthday party. This young gentleman dazzled the crowd with his phenomenal performance. He had everyone on their feet dancing away and singing along. He took song requests, as well as creating and performing an original song special for the birthday queen. Fit for a queen, he brought a beautiful bouquet of flowers to present to my mom, as well as a personalized Polaroid autographed photo to remember this once-in-a-lifetime experience. We especially enjoyed Troy’s Dean Martin impersonations. Troy made my mom’s 80th a spectacular event! He was wonderful!!
Troy put on a spectacular performance for my mom’s 90th birthday celebration with 60 people attending. He arrived on time, he dressed in a tuxedo and absolute captivated the crowd! He sang all the songs we requested, hammed it up with us all and had an infectious personality. Handsome young man who won’t disappoint!!
Dean Martin Impersonator, Frank Sinatra Impersonator, Italian Entertainment
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Such kind words! I had a fantastic time as well it was really enjoyable meeting all of you and to see Lois really drinking it in! It was my pleasure.
What can I say? Troy was just as I had HOPED! I hired him for my mother's 80th birthday surprise party. He arrived on time and she was not only surprised by the party, but that this handsome young man was crooning her! It was incredibly funny, she was dancing with him in the aisle, and she looked up at him and said "wow, you're handsome". He gave us some extra time and sang during our dinner and after! He was a lot of fun and funny!
Troy, I hope you are surviving well after hurricane Ian!?
Dean Martin Impersonator, Frank Sinatra Impersonator, Las Vegas Style Entertainment, Singing Telegram, Crooner
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thanks a billion Scott you are a great guy setting up that party and it was pleasure to meet you! Stay in touch my man!
I could not attend, but the person this was for, was delighted. He was flexible on where and how long he was singing, and his personality was great for the group. He performed for 2 hours!
Since I could not attend, I requested a recording of the event, which "Elvis" did send to me - He had the performance broken down into clips that are manageable and can be sent to other friends. Great job!
I found Troy online and we (my family) couldn’t be happier! We had a 95th birthday party for my grandma at my brothers house. She was so happy and surprised smiling ear to ear! She even danced! His performance was top notch, and was just perfect! Troy was very accommodating, I live in Pa and was not at the event in Florida but I gave him my brothers contact info and he was great about keeping in touch with him! He arrived on time and was great! I don’t think my gram wanted him to leave!! He definitely made her birthday a memorable moment for us!!
My husband did not want a DJ for his 80 years old birthday party. As he is a big fan of the Rat Pack I found Troy online , with great reviews from his performance. He didn’t disappoint. Showed up dressed in a tuxedo and surprised my husband with a first song.
Then he set his equipment and sang for one hour creating a big dancing party even with the young crowd that attended my husband’s party!! Thank you Troy for making my husband’s party so unforgettable!!
Rat Pack Tribute Show
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
I had a great time myself and got to meet you wonderful people, thank you so much Isabela what an amazing review.
We had a 90 year old singer at our grocery store. who sings happy birthday to all birthday people. We talked to Troy told him that Joe was a retired opera singer. when Troy came he was perfect. Great singer nice voice and a very nice guy. Made Joe's day.
Italian Entertainment, Singing Telegram
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thank you so much Margaret you just made my day! It was my pleasure!
My dad unfortunately had to spend his 80th birthday in the hospital. Troy was the best gift we could have ever gotten my dad. My dad had a blast and thought he was awesome! Great singer and entertainer. Everyone said it was the greatest gift!
Side note - Troy is a very compassionate person and it showed in the way he communicated with me regarding my dad and and planning this event in a hospital setting.
I would definitely hire him again!
Singing Telegram, Crooner
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Wow what a sweet and thoughtful review. Tremendously kind words, thank you so much Diane it was an honor and a privilege to bring some joy to you Dad and the group.
God Bless,
Troy Chiappone
He is perfect for parties and events. Very professional and has a great voice. Not overly rambunctious and has a clam inviting demeanor about him. Hired him for a small birthday party and he was ah hit.
Frank Sinatra Impersonator, Singing Telegram
My mother was pleasantly surprised to hear the beautiful music of her era being sung by the talented and handsome Troy Chiappone. He went above and beyond in advance of our event to learn a song that was meaningful to my mother to sing to her on her milestone birthday, which happened to fall on Mother's Day this year. Troy made the effort to set up all the equipment the day before the event to make sure everything was ready in advance and to make everything run smoothly. His charismatic presence made our event memorable and entertaining. He brings a youthful energy and spirit to the sound of the classics from the 50s.
Rat Pack Tribute Show
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
It was an absolute pleasure and a beautiful experience to meet your family Lisa and I feel so lucky that I made your lovely event memorable. You are a wonderful and kind hostess.
Sincerely and with love,
Troy Chiappone
Troy was generous with his performance and time. Roamed around the house and deck singing and engaging the guests. We all had fun!
Frank Sinatra Impersonator
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thank you so much Debbie you are a sweet and generous soul. I had fun as well! Great group!
Troy did an excellent job !!!
Frank Sinatra Impersonator
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thank you so much Tony! You rock! Beautiful family I had a fun time!
Troy did an amazing job performing at our NYE celebration. He had a wonderful presence and captivated the audience with his beautiful voice. We will absolutely be welcoming Troy back to our event next year, and we plan to put him in front of a much larger audience!
Frank Sinatra Impersonator, Crooner
Response from Troy Chiappone sings Sinatra, Dean Martin, Elvis, and more!:
Thank you so much Jamie! You are a very professional and hard working woman!
God Bless You! and see you next year for an even more fantastic show!
Sincerely,
Entertainer and Professional Vocalist-- Troy Chiappone
Troy was very entertaining and kept the party lively especially with the women. He made my wife's birthday party very special.
Crooner
Troy was the hit of our party. A very talented young crooner with personality and a gifted voice!
Songs from Frank Sinatra, Dean Martin, and Elvis gave our event a special ambiance. Thanks again, Troy.
Crooner
Booking Info
Price Range: Contact for rates
Gig Length: 10 - 180 minutes
Languages: English
What to Expect
Regarding Singing Telegrams,
For singing telegrams I bring my portable Bose speaker system and wireless microphone where I can walk right up singing with excellent sound as soon as I arrive and pleasantly surprise your special someone!
I usually sing 1-3 of the best songs from my set-list such as: "New York New York", "Fly me to the Moon", "The Way you Look Tonight", "Can't Help Falling in Love -Elvis Presley", "Margaritaville", "Folsom Prison Blues", etc.
I usually sing happy birthday after a few songs or when the timing is right.
(If you have any requests or preferred songs let me know!)
I usually dress sharp in a 007 style tuxedo or otherwise. I make it very personalized and fun. I am not afraid to walk right up to your special someone or sit next to them and serenade them (lots of smiles guaranteed ;)).
I don't make it only about myself either, I center it around your special someone and even share the microphone if they are the type that wants to show off a little and sing too which some people have really enjoyed from experience. I really try to engage the audience and make it an amazing memory.
*For those who desire an even more luxurious experience, I offer a deluxe singing telegram package where I can bring a bouquet of flowers and/or wine and other personalized gifts (given enough notice ahead of time) delivered in an autographed gift bag. We can even take selfies together and print them out instantly so that you can hold onto the memory for years to come. Prices vary based on how far ahead I am notified and the complexity of the gifts requested.
Regarding One, Two, or Three-Hour Performances (or Anything in Between),
-For a three-hour-show I usually take one or two 15-20 minute breaks to break up the set-list, make special announcements, or take pictures with the party. My set-list involves dozens of my best songs and I cycle through the music various legendary artists, usually performing a handful of Frank Sinatra's songs, then Dean Martin, the music of Tom Jones, Elvis Presley, Johnny Cash, Select country songs, Jimmy Buffett, Elvis Presley, or whatever I artistically feel the crowd may enjoy most in the moment.
-For a one-hour-show or less I usually perform straight through, singing a solid set of songs.
- I always show up on time so I can set everything up perfectly, I bring a robust speaker system appropriate to the size of the venue and the requests of my clients.
- I am one of few performers who utilizes wireless speaker technology so that I can walk around with my wireless microphone inside or even outside your private house party singing, and with speakers strategically placed so that everyone can hear me even in separated rooms. I interact with your guests so that I am not just stuck in one area which allows for a lot more fun, entertainment, and an intimate show. I try to really engage with people and make them feel special when I walk up to them or sing nearby them.
- From the way I dress to the presentation of my equipment, my setup is clean, sophisticated, and looks classy with black cloth table covers and black speaker-stand tripod skirt-skrims.
- I even have an (optional) impressive dance party light that I mount on a 12 foot tripod if my party wants to have a dance after party for an hour after my show. I have dance music playlists via spotify and may take requests like a DJ if that service is requested.
About
I was born and raised in the country of upstate NY and moved to Punta Gorda, Florida in 2021 when I was 27. In my free time I enjoy permaculture gardening, caring for my tropical fruit trees, hunting, fishing, swimming, running, and playing tennis with my brother. I appreciate and love the music of timeless artists, especially: Frank Sinatra, Elvis Presley, Dean Martin, Sammy Davis Jr., Bobby Darin, Jimmy Buffett, Tom Jones, Johnny Cash, and Josh Turner. I am of Italian and other European heritage, however I am a proud American citizen and lived in these United States all my life... I do love me some good coffee and a fresh cannoli, seafood pasta with red sauce, the song "My Way", and the company of gorgeous women and friends, "Nothing but the best is good enough for me..." as the Sinatra song goes. I love traveling throughout the beautiful state of Florida and this great country. Currently, I am not married and have no kids, although that is certainly a possibility in the near future. In the meantime, I'll focus on the music and I'll say cheers to more good times to come! I love meeting the people at my performances and I feel blessed to make people happy with my talents.
Additional Booking Notes
I bring all of my own equipment. The equipment that I choose to bring varies based on the venue size and layout. Key components are: my high-end wireless microphone, my instrumental music tracks that accompany my voice, my compact but powerful line array speaker, or multiple speakers for larger or oddly shaped venues where I can still deliver excellent sound.
All I need is a power outlet and a small space to put my speaker for private parties, I can for example, sing around your pool and also inside your house at the same time with my wireless speaker technology.
For a surprise event (singing telegram) at a restaurant table or special location such as at someones workplace or home I bring a portable Bose Speaker and sing over instrumental tracks. I hold a wireless microphone in my other hand, and the best part is that I sound great with zero setup time!
I also have lighting that I can bring upon request for dimly lit venues or for other reasons.
I even have an impressive party light for an after-singing dance-party (upon request) where I can do a little DJ'ing with Spotify and Youtube playlists.
Set List
Some Highlights Include...
Fly Me to the Moon
New York New York
Come Fly With Me
My Way
That's Amore
An Evening in Roma
All Shook Up -Elvis
Love Me Tender
Can't Help Falling in Love
The Way You Look Tonight
Margaritaville
Five O'Clock Somewhere
It's Not Unusual
Moon River
Mack The Knife
and much more...
Influences & Inspiration
Frank Sinatra, Dean Martin, Michael Buble, Jimmy Buffet, Elvis Presley, Bobby Darin, Tom Jones, various pop and country music artists.
Setup Requirements
Power Outlet (may not even be necessary in some cases)
At least a small space to perform
I don't require anything for Singing Telegrams (no setup required I have battery powered equipment)